Two times Tsunade won a bet and one time she didn't
by FissionPowered
Summary: "You've never won any of your bets!" Jiraiya grinned. But even Tsunade, legendary not only as one of the Sannin but also for her lack of gambling prowess, won her bets sometimes. Thought she had lost so, so much.
1. Prologue: The Departure

**Two times Tsunade won a bet and one time she didn't**

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_**Author's Note: **A Naruto fic, at long last! I really like this ship though it tends to be sad…and so dead, literally. Oh well, I still wrote this because I had a lot of feelings about it and wanted to write some fan fiction. I'll warn you, this fic jumps around a lot in terms of timeline. It's pretty much chronological, except for this prologue. The story is pretty much what actually happened with Tsunade and Jiraiya, with some added things to sort of…fill the gaps. It also attempts to center around some important moments they had together. Hope you like it!_

_**Disclaimer: **I do not own Naruto or any of these characters; if I did it would be called Madara and this ship would be canon._

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**Prologue**

Evening was settling into Konoha. The sun was sinking down behind the Hokage Monument, and lights started to flicker on in windows. Tsunade and Jiraiya sat on a bench at the edge of the village and watched the transition from day to night. It would have been almost romantic save for the somber mood that hung in the air between them. A little while earlier they had been talking, exchanging memories and recalling simpler times, but they'd fallen silent now. Tsunade still felt a bit woozy from all the sake she had drunken hours before. A street lamp blinked to life above the pair, bathing them in yellow, and suddenly Jiraiya stood.

"Well…I'd better be heading out." He picked up his scroll of seals from beside the bench. Tsunade clenched her robe in her hand.

"You realize that you'll be heading straight into enemy territory, to face the leader of the Akatsuki? To be able to control that whole organization…he must be a very powerful ninja." she paused and gathered herself, "So, please, please Jiraiya. Come back alive."

He looked at her. Tsunade was the Hokage, and woman known across the ninja world as one of the Legendary Sannin, as well as for her amazing medical ninjutsu. There was no doubt, at least in his mind, that she was a strong kunoichi. In that moment, though, she looked so fragile: her body hunched, her arms thin and pale against the rich green of her robes. Her small body was the container of much pain.

"If I lost you too," she continued, not meeting his eyes, " I'd…I'd-"

"What? You'd cry for me? That'd make me happy," he smiled, "But I doubt it would be the same as when Dan died."

"You idiot," said Tsunade under her breath, gritting her teeth. Of course it wouldn't be the same." Jiraiya chuckled.

"If you're so worried about it, then why not make a bet with me?" he asked, and she glanced wearily up.

"What?"

"You bet that I will die."

There was a sudden intake of breath, and Tsunade's eyes widened.

"Why?" she whispered.

"Because, after all, you've never won any of your bets!" Jiraiya grinned slyly before suddenly becoming serious.

"But, Tsunade, if I do make it back alive…"

He looked at her pointedly, the question clear in his black eyes. She returned his gaze unsurely. It had been the same request for years, and if he had asked her at any other time he would have undoubtedly received a chakra-enhanced punch to the face, but this time all Tsunade could do was stare in shock at her former teammate.

"Joking, I'm just joking, " Jiraiya laughed, trying to defuse the situation, and Tsunade looked down again.

"Don't feel bad," he reassured, "I'm used to rejection. Ever since we were Genin you've been calling me an idiot, and I guess I was an idiot back then. But every time you called me that, it just made me stronger, and I learned to laugh it off."

Jiraiya paused and pulled out one of his _Icha Icha_ books. "I even managed to make a joke out of it. Rejection made me stronger."

Tsunade smiled a smile that didn't quite reach her eyes, but remained silent. It was an understanding silence, an assuring silence that hung in the air between them. The two had grown up together, trained together, and what he said was true. She _had_ always called him an idiot, warranted or not. Even now, the word rolled naturally off her tongue.

"It's getting late," Jiraiya sighed, "I really should be on my way now."

"Yes," mumbled Tsunade. Of all the things she could have said. She couldn't manage anything else. Not even "be safe."

The Toad Sage turned and strapped his scroll to his back, and walked away from the Hokage, his wooden sandals clacking against the pavement. Without turning around, he raised his hand, giving her a thumbs up.

"Farewell."

As she watched him walking off into the distance, his long shadow getting further and further away, she placed her bet and hoped with all her soul that she wouldn't win.

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_And done! With the prologue at least. I know this part was basically just what actually happened in the manga/anime, but I promise later on there is more interesting stuff. This is planned to be about five chapters, longer than this mostly, so stay tuned. And tell me what you thought? Until next time._

** -FissionPowered.**


	2. Chapter 1: The Bell Test

_**Author's note: **Here is the next (well, technically first) chapter! It jumps back in time considerably from the prologue, and it's based on the actual first day of training that Team Hiruzen actually did._

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**Chapter One**

In the early morning light, the windswept grass of the training field rippled. Tsunade bounced up and down on her toes, peering out across the field, ready to begin her very first session of official ninja training with her new sensei and teammates.

None of the aforementioned persons had appeared on the scene, however, so she was left sitting on her own at the edge of the field. Excitement boiled in the pit of her stomach. Or maybe that was hunger. Probably the latter. She had not eaten breakfast; in fact she had specifically been instructed not to. Instead she'd brought a lunch with her, thinking she might need it after training. But since no one had bothered to show up and commence said training, the blonde reached for the small package at her side and began to unwrap the meal.

The sky was clear. The food was good. Tsunade sighed. Despite the fact that she was still alone in the training area, she felt an increased sense of hopefulness. Today would be the day her journey along the road to being a true ninja would begin. Again she looked out across the field. In roughly the middle, three wooden poles suck out of the earth. Tsunade didn't know what purpose they served, but she didn't get much time to ponder it. A party of three was approaching from the east. The would-be kunoichi stood up abruptly and brushed herself off. Surely these were her teammates.

The group, as far as Tsunade could see, was composed of Hiruzen Sarutobi, the Third Hokage, who was to be her sensei, and two other boys who walked along at his side. One had a shock of white hair, but the other had straight, black locks. The three of them stopped in front of the logs in the middle of the field. Hiruzen, who had apparently noticed Tsunade making her way towards them, waved at her.

"Hello Tsunade," he said when she came to a stop, "I see you arrived here early. I apologize for my tardiness, however there was…well, an _issue_ which was in need of resolving." The two boys gave each other pointed glares.

"Don't apologize," replied Tsunade cheerfully, "I'm just pleased to be here."

"We might as well start," Hiruzen sighed, "Now would probably be a good time for introductions. Why don't you tell each other your names and a little bit about yourselves?"

The three would-be Genin stared at each other in silence for a few seconds, silently sizing up their competition. Tsunade spoke first.

"I'm Tsunade Senju," she said, pride accenting her voice, "And I'm gonna be the greatest kunoichi the world has ever seen!"

Again there was silence. Then, the white haired boy strode up to Tsunade and stuck out his hand.

"Nice to meet you. I'm Jiraiya! You can send me a love letter later!" he grinned at her, eyes sparkling.

"Whatever," she said, looking away, "I don't much care for you."

"Pffhe…" Jiraiya slowly dropped his hand, his smile evaporating, "It's not like I'd want to associate with a flat-chested girl like you anyway."

"What did you just say about me, you perverted brat?" Tsunade spun around and glared at him, fists clenched.

"Hey!" reprimanded their sensei. "We've just gotten here. Could you try not to argue? And Jiraiya…please don't start anything with Tsunade."

"Yeah," said Jiraiya, looking down.

"What about you?" asked Hiruzen, looking over at the black haired boy.

"My name is Orochimaru," he rasped, pausing for a second as if considering whether he should go on, "My goal is to learn every jutsu in the world."

"A very admirable goal," said Hiruzen, obviously pleased with this answer, "Now that you're all acquainted with each other, why don't we start with the training, huh?"

"Finally!" Jiraiya pumped a fist in the air. Tsunade looked at him disapprovingly, but inside she mirrored him. She too was happy to get started.

"The first thing on the agenda is actually a test," started Hiruzen as he reached into his pocket and extracted two small silver bells, which jingled as he moved them, "The objective is to take these bells from me. However, as you can see, there are two of them and three of you. This means that …"

"One of us will end up without a bell." finished Orochimaru.

"Very good inference, Orochimaru. Well done." said Hiruzen approvingly.

"Hey, Tsunade, if I get one of those bells, then you will go out with me?" asked Jiraiya.

"If you don't, then you'll stop bothering me about it."

"You want to bet?"

"Why not?"

"Alright! I'll do it!" said Jiraiya with newfound enthusiasm. He was just about to attack when Hiruzen disappeared into a cloud of smoke.

"What?" shrieked the white haired boy, "He can't just challenge us and then leave!"

"He's still somewhere in the vicinity," said Orochimaru dismissively, "we just have to find him."

The three split, setting out to look for their sensei. Tsunade slipped through the forest at the edge of the field. Focusing her mind on stealth, she snuck around trees and dodged behind bushes, until finally she came upon a small clearing. Peeking out from behind a tree she saw Hiruzen sitting on the ground, reading a book. He had his back to her, and Tsunade, overtaken buy a surge of ambition, was about to rush forward before she noticed something shiny just below her eye level. The metal strings were almost invisible, but if she ran into them it would be a dead giveaway of her presence and would completely nullify her chances at a sneak attack.

As far as she could see, the wires were wrapped around the whole perimeter of the clearing. Her sensei was obviously prepared, so Tsunade opted to climb a tree and attack from above. Not yet proficient enough in chakra control as to be able to simply walk up the trunk, she had to scale the nearest tree hand over hand, grabbing onto branches until she was high up enough to have a clear view. Astounded that the noise she had made climbing the tree had not already alerted Hiruzen to her presence, she inched out along a branch, reaching for a kunai. Pulling one from her pocket, she grasped it and then leapt from the tree.

As soon as her feet left the branch, Hiruzen looked up and saw his trainee descending upon him. Swiftly he pulled out a kunai to counter Tsunade's oncoming attack. Student and teacher met with a clang of metal. Tsunade tried to reach for one of the bells dangling from Hiruzen's belt, but he sprang out of reach. Annoyed, she pulled four shuriken from a pouch attached to her leg and hurled them at her sensei. He dodged them with ease, but this gave Tsunade time to run up and engage him in hand-to-hand combat.

She threw a punch at him, but he simply put up his hand to block it.

"Taijutsu, Tsunade?" he asked, amused. She reached up and grabbed his hand, quickly pulling his arm down and kneeing him in the chest. He grunted, but pushed her away with his other arm. Undeterred, Tsunade came at him with a series of well-executed kicks aimed at his head and chest. Hiruzen blocked all of them, as Tsunade knew he would, but he still took a step back. She smiled.

Tsunade continued to attack her sensei with punches and kicks, most of them being ineffectual, however they all served one purpose: to drive him to the edge of the clearing. It wasn't something Tsunade was sure would work, but if she could get him to trip or hesitate for even one second because of that wire, she could grab one of the bells.

They were getting closer. Tsunade once again pulled out her kunai, slashing directly at her sensei's face. He moved to the side, but Tsunade brought the kunai down, forcing him to move again. He hadn't looked behind him, and at that second his ankle connected with the wire.

He didn't trip. He didn't fall backwards, in fact, he didn't move at all. Tsunade lunged for the bells, but before she could grab them, a smoke bomb went off.

It was not something she had intended to happen. She couldn't even see where Hiruzen was, but there was no doubt he had escaped her reach by now. All she heard was the tapping of sandals against the earth, and somebody shot past her. There was the screech of metal on metal, followed by a faint jingle of the bells, and then nothing.

_Damnit_.

As the smoke cleared, Tsunade readied herself, clutching her kunai in one hand and few shuriken. At that moment she wished she knew more techniques, but she was armed with only with her academy knowledge and ninja tools. Looking around, she tried to locate her sensei again.

To her surprise, Hiruzen was still there, only this time he was perched in a tree above her. He had gone back to reading his book. Tsunade flung a shuriken at him, and Hiruzen was about to move to dodge it, but it didn't even come close enough to graze him. Instead, the shuriken lodged itself firmly into the branch a few feet away. He looked down at her expectantly.

"Well?" he asked. She didn't move. She didn't even reply. He withdrew a kunai from his pouch and threw it at her, assuming she would dodge. But she didn't.

The second the sharp blade made contact, Tsunade exploded from the shuriken behind her sensei, diving forward and grasping for the one remaining bell. Her fingers closed around it, and she jumped back, yanking it from Hiruzen's belt. The clone in the clearing went up in a cloud of smoke. She stumbled back along the branch, trying to catch her balance. Hiruzen looked down, and then slowly broke into a smile.

"Well done, Tsunade," he said, "Well done indeed. Very effective use of the transformation technique."

She was out of breath, but she grinned widely. She'd actually done it, wrested the bell from a ninja many ranks above herself. She'd completed the test.

"Who got the other one?" she asked, although she was almost sure she already knew.

"Orochimaru," confirmed Hiruzen, "He was the one who threw that smoke bomb."

"We should probably go and see how Jiraiya is getting on," laughed Tsunade. She had been right. Her other teammate hadn't gotten a bell after all.

"Ah…well, yes."

And so it was that Jiraiya ended up tied to the log without a bell or a lunch while Tsunade dangled her hard won prize just out of his reach.

"It seems like I've won this bet, Jir-ai-ya," she gloated.

"Shut it, plywood chest!" he said, grinding his teeth.

"Did you just-"

"Stop that!" said Hiruzen, before Tsunade could beat Jiraiya to a pulp, "You are now all a team, and if you want to be successful, you must learn to work together rather than insult each other."

Jiraiya pouted, and Tsunade crossed her arms, but the two ceased throwing insults. It was a fragile peace, one that could be broken by a simple misplaced comment from Jiraiya, but it held for the most part. Tsunade grew used to her white haired teammate, and they formed a tentative friendship. Slowly, very slowly, Tsunade began to realize that maybe, just maybe, he wasn't as much of an idiot as she had thought.

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_**A/N:** If you're wondering what even happened with Tsunade and how she got the bell, I'll explain it here. It was a bit tough to come up with a realistic plan using only E-rank techniques but this was what happened: Tsunade made a clone but also used the transformation technique on herself in order to take the shape of a shuriken, which she had the clone throw. Hiruzen didn't realize this, so while he was distracted with the clone, Tsunade released her transformation (since she had gone from the ground to the tree unassumingly) and grabbed the bell. I hope you liked this part! Tell me what you thought, positive or negative, anything really, I'd love to hear it._


	3. Chapter 2: The Necklace

**Chapter Two**

"I'm going on my first mission tomorrow!" cried Nawaki excitedly as he ran across the roof of the Hokage's headquarters towards Tsunade. She turned and smiled at her brother, recalling her excitement when she and her teammates had been assigned their first mission. It had been years ago, and she had since become a Jounin. Other things had changed too. Tsunade felt a pang of worry at the thought of her little brother going off on a potentially dangerous mission.

"I'm sure it'll go well. You're one step closer to being a great ninja," she said, trying to both encourage him and banish her fears.

"A great ninja? I'm one step closer to being the Hokage, you mean!" he grinned, "To be Hokage is my dream! I'll be the one to protect this village!"

"Well, if you want to be the best Hokage, you still have to be a great ninja, right? How else are you going to keep the village safe? Grandfather was certainly a great ninja," replied Tsunade, pointing at the Hokage Monument above them. Her other hand went to the turquoise stone necklace she wore. Hashirama Senju, the First Hokage, their grandfather, had given it to her as a gift shortly before his death years ago. She wasn't sure why he had given it to her, but she felt it had some kind of significance. Slowly, Tsunade unclasped it and turned to Nawaki, dangling it in front of his face.

"I want you to have this," she said.

"Huh?"

"I want you to have it. It belonged to the First Hokage, and now it'll belong to you, the future Hokage!" she said, smiling, "Just think of it as a birthday present from me. And Hashirama."

The look of confusion on Nawaki's face turned to glee. "Aw, that's so cool!"

"Come here," Tsunade said, beckoning him forward. She hung the necklace around his neck. After adjusting it a bit, she took a step back.

"You look great," she proclaimed, "like a Hokage already!"

"Really?"

"Really really."

"Thanks. I'll keep it safe!" he said, and she hugged him. She wanted to hold him like that forever, just to keep him safe, but she knew she couldn't, she knew –

"Ow, Tsunade, you're squishing me!" he yelped, and she relinquished her hold.

"Sorry. I guess I got a little carried away," she said, "But you're gonna have to deal with bigger issues than tight hugs before you become Hokage!"

She tousled his hair, and he grinned before turning to leave.

"I gotta go get in some last minute training before the mission," said Nawaki seriously, "I want to be prepared."

"Sounds good." Tsunade was secretly grateful he was taking this at least somewhat seriously. He ran off, and she leaned against the roof railings, looking out across the village.

Tsunade stood in the doorway of the hospital room, panting hard, water dripping from her hair, looking on as two doctors milled about a body that was mostly covered in sheets. She was too late. Too late.

Her former teammates stood before her, flanking the door. Their clothes were wet, and Jiraiya's normally spiky hair was slicked down with water. His eyebrows were drawn together with concern, but Orochimaru looked completely unfazed. Tsunade made to enter the room. She had to see her little brother.

"Tsunade," said Jiraiya, putting his hand on her shoulder, "It's better if you don't."

"Why not?" said Orochimaru, flicking his eyes towards the room, "She won't be able to identify him anyway, the wounds were so bad, and since there are no medical nin-"

"That's enough." Jiraiya turned towards Orochimaru, daring him to say more. Tsunade stepped backwards, lowering herself onto a nearby bench.

"Well," continued the dark haired man, "We are at war, are we not? This is what happens. Especially when children get over ambitious."

"Orochim-"

"Anyway," Orochimaru turned his back on Jiraiya and made his way over to where Tsunade had sat down, "I thought you might want this back."

He pulled her necklace from his robes, and set it swinging back and forth on one of his fingers. Tsunade looked up, glossed eyes widening.

"Give me that." she growled, reaching to snatch it from him.

"There's no need to get touchy, I just thought you would want that trinket returned." said Orochimaru, his voice unsympathetic, "Though it is a pity, considering how recently it was bestowed upon your brother."

"Shut up." Tsunade mumbled, clenching her fist around the necklace protectively, as she retreated back into herself, "Just shut up."

"Well, then, my work here is done," he said as he turned on his heel and walked away, "See you."

Unlike his teammate, Jiraiya was reluctant to leave so soon, and he sat down on the bench next to Tsunade.

She didn't say anything. She couldn't even form words. Her little brother was lying there under all those sheets, and he was dead. Dead, when only yesterday he had been very much alive. He had talked about being Hokage. He had smiled and laughed with her. She had entrusted him with her necklace, the First's necklace, the necklace she believed would somehow protect him, and now he was lying lifeless on some table, and the necklace was back with her. She felt the tears swelling in her eyes, and the knot forming in her throat, and Tsunade turned away, sinking down onto a nearby bench.

"I'm so sorry," said a nurse who had appeared on the scene, her words falling on deaf ears. Tsunade just put her head in her hands and blinked back the wetness filling her eyes. She tried to hold herself together. But it just didn't seem real. That person covered by sheets had to be someone else. Maybe they had made a mistake. Nawaki was fine, he was fine, he was probably heading home right now. Things like this didn't happen, not to her, not to people like her brother. It was all some terrible mistake. A mistake, a mistake, a mistake.

For a while the two of them just sat there, Tsunade gritting her teeth and holding tightly onto the necklace and Jiraiya staring at the floor. Then, slowly, very slowly, he reached out a hand and tentatively placed it on her shoulder. Tsunade didn't object, but rather started crying in earnest, her tears finally breaking free. Jiraiya quickly removed his hand, thinking he had done something wrong.

"No," sobbed Tsunade, reaching out for his hand, "Don't."

She interlocked her fingers with his, squeezing tightly. Jiraiya, still trying to tread lightly, stayed frozen. To his surprise, Tsunade turned and rested her head on his shoulder, burying her face in his already soaked robe.

Jiraiya had never been particularly good with comforting people, and he was even worse with words around Tsunade. So instead he turned and wrapped his arms around her, pulling her close.

"It'll be okay," he managed, "It'll be okay, Tsunade."

Tsunade continued sobbing, and he patted her back slowly. They sat on the bench like that for hours, until Jiraiya's arms grew stiff and Tsunade's tears dried around her swollen eyes. She took a deep breath and shakily rose to her feet. Jiraiya jumped up to support her, and she leaned on him as they walked out.

"Thank you" she said as they stood on the hospital steps, breathing in the damp air, "Thank you for staying."

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**A/N:** _Thanks so much for reading! I'll try to put a new chapter up soon, but I'm still working on it. A review for this one would make my day, though. Seriously, tell me what I'm doing well, or what I'm not doing so well. I want to make this the best story I can for you guys and I can't do it without your help!_


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